The REWORK podcast

A podcast about a better way to work and run your business. We bring you stories and unconventional wisdom from Basecamp’s co-founders and other business owners.


Living on Hope

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We call up our friend and former colleague Esther Lee, who lives with her husband on a 35-foot sailboat named Hope in Jacksonville, Florida. Esther, an “idealist in hiding,” talks about how living smaller gives her more space to turn outward and care for others, especially now.

The Full Transcript:

Wailin: [00:00:00] It’s really good to see you and hear your voice again. It’s been so long.

Esther: [00:00:04] I know. I was so pleasantly surprised. I was so touched, I mean, I’m so excited and this is definitely the highlight of the week.

Wailin: [00:00:13] Oh my goodness.

Esther: [00:00:14] But especially this week. Oh my God.

Wailin: [00:00:18] I mean…

Esther: [00:00:18] Seriously.

Wailin: [00:00:20] Where to even start? Well, let’s start—how about you introduce yourself and you can say what your name is and what you do?

Esther: [00:00:24] Hi, I’m Esther. I’m a writer, former teacher and now designer and I live and work on a 35-foot sailboat named Hope.

[00:00:34] Broken By Design by Clip Art plays.

Shaun: [00:00:34] Welcome to a bonus episode of Rework, the podcast by Basecamp about the better way to work and run your business. I’m Shaun Hildner.

Wailin: [00:00:41] And I’m Wailin Wong. I don’t know if this has been the case for you, but sheltering in place has motivated me to either reconnect with people or be in touch with them more frequently. Like, I see my parent almost every day and my in-laws every week, all on Zoom. I’m texting a lot more with friends. You and I are even playing way more Dungeons & Dragons.

[00:01:00] There’s something about facing all this collective existential dread that has brought us closer together.

Shaun: [00:01:05] Well, you know my natural response to any upheaval is to hide away in a cold, dark cave. So I can’t totally relate. But in that spirit of connection, you recently got in touch with an old friend, our former Basecamp colleague, Esther Lee. And her stay-at-home situation is a little different than what we’ve been living through here in the big city.

Wailin: [00:01:23] Yeah, she and her husband, Michael, live on a 35-foot sailboat. I wanted to hear about her experience kind of distilling life down to its essentials and living with less in a material sense while building community and caring for others at full tilt. This conversation put wind back in my metaphorical sails and I hope it does the same for you.

[00:01:44] Broken By Design by Clip Art plays.

Wailin: [00:01:53] How did you decide to live on a boat?

Esther: [00:01:55] That was a little bit of a process. It took a couple years, but my husband and I, we started chatting about it. He’s had exposure to sailboats as a young guy on Long Island and also in San Francisco with friends’ boats. It never occurred to him, like, oh, that people could actually live on a boat and that sailing could be more of a regular part of our lives.

[00:02:16] Whereas myself, I had no background in sailing whatsoever. I mean, my parents are, yeah, immigrants. And not that they can’t have sailing experience but they totally… neither of them swim. They’re not interested in sailing. We never went on vacations, so it’s like…

[00:02:33] We started talking about something that felt more aligned with us. We feel in some ways kind of like misfits in a way. And I say that endearingly, and for lack of better term, just meaning like, I think that’s one of the many things that my husband and I feel connected to each other about. And we both had gone through the right steps where, in quotes “right steps.” Where I was in academia, I was going down the whole tenure track road. He was also going to go to into academia in the arts, and then we kind of thought, oh my gosh. The likelihood of us both finding tenure-track jobs in the same city.

[00:03:12] So, just a lot of questions and a lot of upheavals in our families. My mom was diagnosed with Alzheimer’s. So, we just started to question, what could we do that feels more like us and that just began a journey of talking. We eventually watched that documentary, The Minimalists. And we were living in Atlanta at the time. He goes, “You know, I know we’ve been talking about this but what do you think about ramping up our plans, selling our place, getting a boat, but staying close to Atlanta just for a year or two and going from there?”

[00:03:45] And he was really surprised, because I just said, yeah. Let’s do it.

Wailin: [00:03:51] Were you surprised to hear yourself say, yeah, let’s do it?

Esther: [00:03:54] A little bit. But I think there were so many things at play leading up to that point where I was feeling a lot of upheaval and stress and kind of yearning for a change. The decision is super scary. It’s exhilarating and it’s bewildering, but you know what? It’s going to be okay. We’ll either find out we don’t like or we find out we fail and we go to the next thing, and it’s going to be all right.

[00:04:22] So we sold our place, made just enough to buy this boat, 1994 Island Packet 35’, and she needed some work, and that’s why we were able to afford her. And so we moved aboard and did the work as we went, which you know. That has its challenges and hilarity.

Wailin: [00:04:41] And how did you settle on the name?

Esther: [00:04:43] The boat was already named Hope. And Michael and I were kind of, we’re pretty dark humored, especially Michael. And it’s kind of ironic, but in a way, not, too. Because I also feel like, deep, deep, down we’re actually pretty big idealists in hiding. So it felt right. We actually really like that name.

Wailin: [00:05:04] And what was it like to downsize into living in a 35-foot space?

Esther: [00:05:12] Michael and I, we both are artists. I’m from a writing background, and Michael’s photography. And I just bring that up, because especially with the photography, inherently brings in a lot of equipment and that certainly was the case. We had so many books and photography equipment, an enlarger. So downsizing for the most part actually wasn’t too bad. What I found surprising was, we really got a kick of where certain sentimental things were going to go. All the poetry books and stuff, we donated to an arts high school. And that just like, made me so happy and they were just like, “Oh my God! Are you serious?”

[00:05:54] So yeah, I just was like, win-win. Michael’s photography equipment, too, went to cool people and he gave away his records, special, certain records to special friends and so that whole process actually was really kind of lovely.

[00:06:09] I think the hard part about downsizing, I’m trying to think, would be the very 5% that was left. I struggled with it more than Michael. For instance, he was taking a stack of his prints to the dumpster. And I grabbed them. I said, no, no! And he goes, Esther. I have the negatives. It’s going to be okay.

Wailin: [00:06:32] And what was the first kind of big trip that you took on your boat?

Esther: [00:06:37] We’ve kept it pretty local, to be honest, because we were in Atlanta, so we explored the lake. And then when we moved down to Jacksonville, Florida, we had to move from one area called Green Cove Springs to where our home port is now. It’s not that far. It’s only about, 25, 30 miles. But it was… that was a big step for us because we’re kind of launching and sailing and it was kind of on a little bit of a rainy day, so that tested my own anxieties. But it ended up being such a beautiful sail and we were kind of yearning for that because we were just coming out of Green Cove Springs and doing about two or three weeks of work on the boat when it’s on the hard. Which, anybody doesn’t already know, it’s like, on the hard, meaning the boat already is out of the water on these metal stilts.

Wailin: [00:07:31] What does a good sail feel like?

Esther: [00:07:33] I would say, probably. I mean, people would probably disagree depending on the sailing background. But we’ve actually had really great sails on light wind days. Which, a lot of folks who are into sailing, they want to go out when it’s like, 10-15 knot per hour winds, and that’s great. But there have been days where we’re like, you know what? It’s less than five, but let’s go out and try. And there’s a challenge to that, and when you can actually get your sail to catch a little bit of move and still move the boat in very light winds, you feel like such a badass even though nobody else around you cares or would know.

[00:08:12] So for a newbie sailor, those kinds of things feel really, I don’t know. It’s pretty cool and it feels almost like magic in a way, when you’re at this kind of newer stage of learning about sailing and starting to connect the dots.

Wailin: [00:08:27] What has this pandemic felt like in Florida, like in Jacksonville, where you are? How has it played out?

Esther: [00:08:34] I’m a little bit concerned because Florida obviously has a really high percentage of folks who are older and my mom is one of them, and so I’m just… I’m just hoping we’re taking enough precaution and early enough, too, like everyone. I know you and I have emailed about the whole efforts going around across the country to make masks for medical professionals everywhere. And my sister is an ER nurse, so this is particularly personal for me. And she did personally reach out and was like, I’m about to go back to work on Friday, all my coworkers were all freaking out. Can you and other folks start making masks?

[00:09:18] I’m seeing efforts taking place in Florida in different groups, and so that’s really heartening to see.

Wailin: [00:09:25] Do you have a sewing machine to make these masks?

Esther: [00:09:27] It’s a sewing machine called… or made by a company called Sailrite, and they’re really popular in the sailing, boating world. They’re super sturdy. We got lucky and found on eBay.

Wailin: [00:09:43] And so, you use that sewing machine when you need to make repairs or make anything for the boat itself? So it’s built for those kinds of things?

Esther: [00:09:50] Absolutely. Yeah. And you know, it kind of goes back to something we were talking about, too, in terms of life in a small space. That’s been one of the cool lessons for me, is like. Oh, doing X, Y, Z, that’s going to be really hard, or that’s not going to be very plausible, or feasible. But nine times out of ten, it actually works out. I’ve been really surprised. Sewing these masks and cooking really yummy meals or Michael and I both being on this boat working under this pandemic, like all of us are doing. We just make it work, and it works better than, I think, maybe people would think. We just communicate a lot. Everything’s modular, including our bodies. We’re like, oh, you’re going to work over there? Well, I’m going to work over here. You have a meeting at this time, then… Like, right now, he’s being very mindful about this awesome conversation. So he was like, I’m going to plan to go work at the dinghy over at our storage.

[00:10:54] So, yeah. It’s just like, a lot of modularity.

Wailin: [00:10:58] Would you take the boat out on a longer trip or is that not a good idea because you would have to dock somewhere and travel right now is frowned upon?

Esther: [00:11:07] As it turns out, we actually had planned to do that before this pandemic. Our plan was to go out for our first cruising season around March and the plan was to go out just for a couple of months. That was the plan, was to kind of go south, and there’s so much to explore in Florida, alone. All the way down to the Keys. But I think, shortly before the pandemic hit, we ended up changing plans and postponing and saving up more money. And then the pandemic hit, and Michael’s like, wow. Okay. So, it’s kind of made for us.

[00:11:45] But yeah, I think there are some barriers and obstacles for the folks who are cruising right now. Clearly, based on where you’re heading and if there are certain mandates in place, it makes it tricky if you’re trying to provision and get supplies.

Wailin: [00:11:58] Are you doing freelance work right now? How are you balancing the amount of time you spend working on the boat versus working on some of your other projects?

Esther: [00:12:07] Mainly freelancing and by design I’ve been keeping it less than full time. I’m wrapping up a project with Sierra Club right now. We’re developing their first plastic reduction toolkit. So all the chapters around the country are going to be able to use this toolkit to enact successful, hopefully successful, campaigns and ordinances to reduce plastic.

[00:12:34] I’ve never lived somewhere where you could see the tide so directly. So, that’s new for me. Even though I grew up in Florida, we didn’t live near the water so going out into the boat, I literally could—we’re right here. But on the shore here, by the marina, too. Every day, seeing the tide go in and out. On one hand, there’s this beautiful, like, the surface beauty is there, of course. But then, when the tide is low, it’s like, oh my gosh, look at all this trash. It’s really… it’s very sobering.

Wailin: [00:13:07] And you were set to go out on a research expedition all around plastic in the oceans, right?

Esther: [00:13:13] Yeah, I’m super excited about it and like, everything right now, everything is to be determined under this pandemic, of course. As it should be. But yeah, just, maybe a week beforehand, I’d received the really awesome news that… I’d applied to eXXpedition. They’re woman-led multi-disciplinary crew of women sailing around the world to do research about microplastics. And so I was selected to do the João Pessoa, Brazil leg to Barbados. And this would have taken place in January 2021, but I think things are obviously very up in the air there. But you can track them online. There’s a crew out right now and then, I mean, they were already out. But yeah, it’s an amazing, amazing organization and it’s all multi-disciplinary women of different backgrounds. It’s so cool.

Wailin: [00:14:15] Can I ask what your book of poetry is about?

Esther: [00:14:18] Yeah, oh, thank you. Yeah. The second book of poems is titled Sacrificial Metal and they sparked from difference experiences either I’ve personally experienced, or I’ve witnessed of different women of color in particular in academia. And conversations I’d had back when I was still teaching and I ended up having this amazing conversation with a former student. She was a dance minor and she happened to mention this dancer, dance theorist, Rudolf Laban, I’d never heard of. And for whatever reason, I could not stop thinking about that. And so I started just writing this series of poems sparked conceptually about dance and human movement. And I was really questioning at that time, what does it look like when you’re part of a community? What does it feel like, or look like when you feel exiled from a community? And they also kind of morphed into some poems and portraits about experiences with my mom, who’s living with Alzheimer’s and vascular dementia. So, yeah, just thinking about that, too.

Wailin: [00:15:37] Have you been thinking about community a lot, given what’s going on in the world?

Esther: [00:15:42] Absolutely. I hope we all are right now. But yeah. But no, seriously, though, it’s like one of the cool things people may love about something like living on a boat, it certainly gives you the opportunity to learn a lot of self-reliance. And I appreciate that, I do. Like you mentioned the sewing machine. That, just learning that skill, is allowing me to feel like I can provide certain needed tools and comfort for my family. At the same time, it’s pandemic. It’s like, the literal reminder of how connected we are and what can happen to our detriment if we don’t pay attention and look out for each other. So yeah, I’ve been thinking about that a lot and just what can community look like? What does it look like here in a place I have some ties to but we’re kind of new?

Wailin: [00:16:46] Do you want to close this out and read one of your poems?

Esther: [00:16:50] So this is “Labanotation 26.”

as a boat capsizes—

Someone needs to do something, a witness says on the video.

Sometimes you look at your mother and think, someone should do something,

She points at her neck again, showing you tissues in

the waste basket, yellow pools on each one.

She doesn’t remember the tests nor the diagnoses.

The wind was fierce. You don’t want to mess with it.

What if joy, the therapist in your brain asks, is

a recurring utterance simmering beneath our feet

and, like tragedy, it occurs—

undeniably, relentlessly—every day.

 In the dead of night, someone goes under,

 another survives. Your mother,

both tourniquet and artery.

[00:17:41] Broken By Design by Clip Art plays.

Shaun: [00:17:49] Rework is produced by Wailin Wong and me, Shaun Hildner. You can follow Esther and Michael’s adventures on Instagram at @wayfinders_now. They also have a website at Her new book of poetry is called Sacrificial Metal published by Conduit Books and we’ll link to it in our show notes for this episode which you can find at

[00:18:23] Put wind back in my sails…

Wailin: [00:18:25] I was waiting for you to edit that out.

Both: [00:18:29] [laugh]

Shaun: [00:18:29] I would never!